Synthesis of epothilones A and B in solid and solution phase

K. C. Nicolaou, N. Winssinger, J. Pastor, S. Ninkovic, F. Sarabia, Y. He, D. Vourloumis, Z. Yang, Tongzhe Li, P. Giannakakou and E. Hamel
Additional contact information
K. C. Nicolaou: The Scripps Research Institute
N. Winssinger: The Scripps Research Institute
J. Pastor: The Scripps Research Institute
S. Ninkovic: The Scripps Research Institute
F. Sarabia: The Scripps Research Institute
Y. He: The Scripps Research Institute
D. Vourloumis: The Scripps Research Institute
Z. Yang: The Scripps Research Institute
P. Giannakakou: National Institutes of Health
E. Hamel: DCTDC, NCI, Frederick Cancer Research and Development Center

Nature, 1997, vol. 387, issue 6630, 268-272

Abstract: Abstract Epothilones A and B, two compounds that have been recently isolated1 from myxobacterium Sorangium cellulosum strain 90, have generated intense interest2–16 among chemists, biologists and clinicians owing to the structural complexity, unusual mechanism of interaction with micro tubules and anticancer potential of these molecules. Like taxol* (refs 17, 18), they exhibit cytotoxicity against tumour cells by inducing microtubule assembly and stabilization3,4, even in taxol-resistant cell lines. Following the structural elucidation of these molecules by X-ray crystallography in 19961, several syntheses of epothilones A (refs 12–16) and B (ref. 19) have been reported, indicative of the potential importance of these molecules in the cancer field. Here we report the first solid-phase synthesis of epothilone A, the total synthesis of epothilone B, and the generation of a small epothilone library. The solid-phase synthesis applied here to epothilone A could open up new possibilities in natural-product synthesis and, together with solution-phase synthesis of other epothilones, paves the way for the generation of large combinatorial libraries of these important molecules for biological screening.

Date: 1997
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DOI: 10.1038/387268a0

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